(R)-3-phenyl-1-(m-tolyl)prop-2-yn-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-3-phenyl-1-(m-tolyl)prop-2-yn-1-ol
• 英文别名: (R)-1-(3-methylphenyl)-3-phenyl-prop-2-yn-1-ol；(R)-1-(3-methylphenyl)-3-phenyl-2-propyn-1-ol；(R)-1-(3-methylphenyl)-3-phenylprop-2-yn-1-ol；(S)-1-(3-methylphenyl)-3-phenylprop-2-yn-1-ol；1-(3-methylphenyl)-3-phenyl-prop-2-yn-1-ol；1-(3-methylphenyl)-3-phenylprop-2-yn-1-ol；(1R)-1-(3-methylphenyl)-3-phenylprop-2-yn-1-ol
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: IJKKAOUYCHCVQU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙炔 、 3-甲基苯甲醛 在 diethylzinc 、 titanium(IV) isopropylate 、 (S)-1-(4-phenylquinazolin-2-yl)ethanol 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 42.5h， 以98%的产率得到(R)-3-phenyl-1-(m-tolyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes

  摘要：

  Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the optimised reaction conditions, the best enantioselectivity was obtained using L-lactic acid derived 4-phenylquinazolinol and apart from the cyclohexylcarbaldehyde derivative, 16 propargylic alcohols were then synthesised in moderate to excellent enantiomeric excess from 53% to 97%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.067

文献信息

• Simple Derivatives of Natural Amino Acids as Chiral Ligands in the Catalytic Asymmetric Addition of Phenylacetylene to Aldehydes
  作者：Zhi-jian Han、Rui Wang、Yi-feng Zhou、Lei Liu

  DOI：10.1002/ejoc.200400595

  日期：2005.3

  Optically active propargylic alcohols are important chiral building blocks in asymmetric synthesis, and asymmetric addition of terminal alkynes to aldehydes is one of the most important and interesting procedures by which to prepare these chiral building blocks. In this work we have identified some simple derivatives of (S)-proline and other natural amino acids as chiral ligands that can be combined

  旋光炔丙醇是不对称合成中重要的手性结构单元，末端炔烃与醛的不对称加成是制备这些手性结构单元的最重要和最有趣的方法之一。在这项工作中，我们确定了（S）-脯氨酸和其他天然氨基酸的一些简单衍生物作为手性配体，它们可以与 Ti(OiPr)4 结合，然后用于催化乙炔锌的不对称加成，由原位产生苯乙炔与二乙基锌反应生成醛。ee 值高达 90%。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes
  作者：Ramalingam Boobalan、Chinpiao Chen、Gene-Hsian Lee

  DOI：10.1039/c1ob06683h

  日期：——

  series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti(OiPr)4. This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to

  从中合成了一系列席夫碱配体 （1 R）-樟脑。在最佳条件下（+）-SBAIB-a，10被发现是用于对映选择性加成的极好的催化剂苯乙炔 无需使用非手性添加剂或 钛（O i Pr）4。该方法以极高的产率（高达99％）和优异的对映选择性（高达92％）产生了（R）-丙炔醇。相应的（S）-丙炔醇的合成具有良好的对映选择性（高达91％）和极好的收率（高达99％），使用（-）-SBAIB-a，41岁。
• Synthesis of the bifunctional BINOL ligands and their applications in the asymmetric additions to carbonyl compounds
  作者：Ying-Chuan Qin、Lan Liu、Michal Sabat、Lin Pu

  DOI：10.1016/j.tet.2006.06.049

  日期：2006.10

  the diphenylzinc addition which often require the addition of a significant amount of diethylzinc with cooling (or heating) the reaction mixture in order to achieve high enantioselectivity, using (S)-8 needs no additive and gives excellent results at room temperature. (S)-8 in combination with diethylzinc and Ti(OiPr)4 can catalyze the highly enantioselective phenylacetylene addition to aromatic aldehydes

  分别从BINOL和H 8 BINOL与吗啉代甲醇的反应中开发了双功能BINOL和H 8 BINOL配体（S）-6和（S）-8的高效一步合成方法。这些化合物的X射线分析表明它们在结构上有相似之处和不同之处。双功能H 8 BINOL（S）-8已发现对二苯基锌与许多脂族和芳族醛的反应具有很高的对映选择性，尤其是对于线性脂族醛而言，对映选择性最强的催化剂。与开发用于添加二苯锌的其他催化剂不同，该催化剂通常需要在冷却（或加热）的同时添加大量的二乙基锌以实现高对映选择性，使用（S）-8无需添加剂，在室温下可获得优异的结果温度。（S）-8与二乙基锌和Ti（O i Pr）4结合可以催化高度对映选择性的苯乙炔加成芳族醛。尽管对映选择性还不是很高，但它在室温下还可以促进苯乙炔向苯乙酮的添加。在不使用Ti（O i Pr）4和路易斯碱添加剂的情况下，（S）-8与二乙基锌结合可以催化丙酸甲酯与醛的反应，形成高官能度
• Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand
  作者：Hsyueh-Liang Wu、Ping-Yu Wu、Ying-Ni Cheng、Biing-Jiun Uang

  DOI：10.1016/j.tet.2015.07.038

  日期：2016.5

  synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding

  在本文中，描述了手性樟脑衍生的γ-氨基硫醇配体17的设计和合成，以及通过向羰基化合物中添加有机锌试剂在催化对映选择性碳-碳形成反应中的应用。配体17的催化活性和对映选择性通过将各种有机锌试剂对映选择性加成到醛和酮酯中得到证明，从而以高收率和对映选择性提供相应的醇。还讨论了巯基在有机锌与醛的高度对映选择性1,2加成反应中的作用。
• Highly Enantioselective Phenylacetylene Additions to Both Aliphatic and Aromatic Aldehydes
  作者：Ge Gao、David Moore、Ru-Gang Xie、Lin Pu

  DOI：10.1021/ol026921r

  日期：2002.11.1

  The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope

  发现容易获得且便宜的BINOL与Ti（O（i）Pr）（4）结合可催化炔基锌试剂与各种类型的醛反应，包括脂肪族醛，芳族醛和其他α，β-不饱和醛在室温下生成具有91-99％ee的手性炔丙醇。相对于用于该反应的醛的类型，以前的手性催化剂没有表现出如此宽的对映选择性范围。[反应：看文字]